Hydrogen Bromide → HCID 6610498, compound

HRID 2203202Notes

Reaction equation

HRID 2203202 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([N+:10]([O-:12])=[O:11])[C:3]=1N.N([O-])=O.[Na+].[BrH:17]>O>[Br:17][C:3]1[C:5]([N+:10]([O-:12])=[O:11])=[CH:6][C:7]([CH3:9])=[CH:8][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 260Hydrogen Bromide2×HCID 742196-Nitro-2,4-xylidineHCID 23668193Sodium Nitrite

Product 1

HCID 6610498HCID 6610498, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

To a suspension of 2,4-dimethyl-6-nitroaniline (5 g, 30.12 mmol) in water (38 mL) was added HBr (15 mL, 40%). The mixture was heated to reflux for 10 minutes and then cooled to 0° C. A solution of NaNO2 (2.07 g) in water (12 mL) was added dropwise with cooling. The mixture was stirred for 30 minutes and then added slowly to a stirred mixture of CuBr (4.33 g) in HBr (12 mL) and water (23 mL) at RT. The reaction mixture was stirred at RT for 30 minutes, heated to reflux for 3 hours, and then steam distilled. The distillate was extracted with DCM (3×30 mL), washed with aqueous saturated NaHCO3 and saturated NaCl, and concentrated to give the title compound as a solid (1.8 g, 26%). 1H NMR (400 MHz, CDCl3) δ ppm 7.26 (1H, s), 7.17 (1H, s), 2.39 (3H, s), 2.27 (3H, s).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 10 minutes
  3. temperaturewith cooling
  4. stirringThe reaction mixture was stirred at RT for 30 minutes
  5. temperatureheated
  6. temperatureto reflux for 3 hours
  7. distillationsteam distilled
  8. extractionThe distillate was extracted with DCM (3×30 mL)
  9. washwashed with aqueous saturated NaHCO3 and saturated NaCl
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-d681dc61859340d3aaa6375e8215839f
Source dataset
uspto-grants-2016_06
Patent number
US09365566B2

Reaction notes

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